While listening to This American Life recently, I came across the teachings of
Rabbi Maimonides. One of his more famous teachings (and the one mentioned in the episode I was listening to) is the Ladder of Tzedakah (Charity.) In it he enumerates the levels charity from least to most preferred with the intention of encouraging more (and better) charity.
Based on my own experiences with giving I feel like he has a few of these out of order. The anonymity of the gift seems like no big deal whereas the attitude shift between giving grudgingly to giving cheerfully seems like a much more central struggle. That said he's the Rabbi and I'm just the public radio listener...